Sent on August 28, two days after Hurricane Harvey inundated Houston, Trump’s defiant appeal acknowledged the mounting perception that nearly eight months into his first term—and in the aftermath of his racially divisive response to the violence in Charlottesville—he’s never been politically more lonely. He’s at odds with Congress—including leaders and members of his own party—and his deal-making with Democrats is angering some of his most ardent conservative supporters. He’s been abandoned and censured by art leaders, business leaders and world leaders. His Mar-a-Lago resort in Florida is bleeding bookings. And he’s losing favored aides due to the actions of his own chief of staff, General John Kelly, who restricts access to the president with the diligence of a border guard. Last week, the New York Timesdescribed Trump as a “solitary cowboy,” reminding readers he once called himself “the Lone Ranger.”

His critics might see his growing isolation as a product of his political inexperience—an aversion to the norms of the legislative process, a penchant for topsy-turvy management. But as unprecedented as this might be in the annals of the West Wing, it’s merely a continuation of a lifelong pattern of behavior for Trump. Take away the Pennsylvania Avenue address, the never-ending list of domestic and international crises, and the couldn’t-be-higher geopolitical stakes—and this looks very much like … Trump throughout his entire existence. Isolated is how he’s always operated.

The middle son of a stony, workaholic father with whom he had an “almost businesslike” relationship, Trump is a double divorcee, a boss with a professed distaste for having partners or shareholders, a television-tethered, hamburger-eating homebody and a germaphobe who has described shaking hands as “terrible,” “barbaric” and “one of the curses of American society.” He’s been a loner most of his life. At New York Military Academy, everybody knew him but few of his fellow cadets knew him well. In college, he made no friends he kept. After he moved to Manhattan, he lived in a sealed-off triplex penthouse, relied on a small, family-first cadre of loyalists and mainly made more enemies than allies (the mayor was a “moron,” elite “so-called social scene” types were “extremely unattractive people,” and on and on). At his casinos in Atlantic City, he was adamant about not mingling with the gambling masses. Now, in Washington, he’s a two-scoopscable-watcher inside the White House when he’s not weekending at his clutch of protective, name-branded bubbles. Trump, forever, has collected an array of acquaintances, fellow celebrities and photo-op props, while friendships mostly have been interchangeable, temporary and transactional.

Trump waves while speaking outside of the Annaville Fire House after attending a briefing on Hurricane Harvey in Corpus Christi, Texas, on August 29, 2017. | JIM WATSON/AFP/Getty Images

“He was and is a lonely man,” Jack O’Donnell, a former Trump casino executive, told me.

“One of the loneliest people I’ve ever met,” biographer Tim O’Brien said in an interview. “He lacks the emotional and sort of psychological architecture a person needs to build deep relationships with other people.”

It’s been this way always, because he’s always been foundationally, virulently untrusting. “There’s a wall Donald has that he never lets people penetrate,” a former associate told me. Trump has a dark, dour view of humanity. He considers the world “ruthless,” “brutal” and “cruel.” Through this zero-sum, dog-eat-dog lens, friends aren’t friends—there’s no such thing. “They act nice to your face, but underneath they’re out to kill you,” he wrote in his 2007 book, Think Big. “… they want your job, they want your house, they want your money, they want your wife …” Why he’s like this is the subject of vigorous discussion among psychology experts. The deep-seated influence of his formidable father? The wound of the alcohol-fueled death of his more mild-mannered older brother? Simple genetics? Trump is not self-reflective—“I don’t like to analyze myself because I might not like what I see,” he told a biographer several years back—but he can be self-aware. And on this front, he’s been quite clear, and remarkably consistent.

“My business is so all-encompassing I don’t really get the pleasure of being with friends that much, frankly,” he said to one interviewer in 1980.

“Most of my friendships are business-related because those are the only people I meet,” he said to another 36 years later. “I think I have a lot of friends, and some of the friends I haven’t spoken to in many years. … I mean, I think I have a lot of friends, but they’re not friends like perhaps other people have friends, where they’re together all the time …”

Exceptions exist, of course, and Roger Stone is one of them. The inimitable, provocative political operative has known Trump, and has been friends with Trump, since 1979, when Stone was working on Ronald Reagan’s presidential campaign and Roy Cohn introduced him to Trump. “It’s fun to be his friend,” Stone told me. Few people have known Trump longer than Stone, or know him better.

“By definition,” Stone said, “I think anyone who has the job is going to be lonely. … Lincoln wrote extensively about the loneliness of the job.”

Roger Stone is an exception to Trump’s isolation; the two have been friends since 1979. | Getty

But Trump, well before he was elected to inhabit the Oval Office, was “psychologically lonely and isolated, emotionally lonely and isolated,” I suggested to Stone. He’s a person who certainly can be socially gregarious and charming—many people say that, because many people have experienced it—but he ultimately prefers to be on his own, I offered. Now that he’s president, it seems these “self-isolating” tendencies have been exacerbated. I wondered if Stone agreed.

“I think,” Stone said, “that’s generally true, yes.”

There’s been so much focus, understandably and unavoidably, on the various parts of Trump’s personality that have helped define his presidency to this point. They are frequently cited as obstacles to his and his administration’s success. His driving belligerence. His fleeting attention span. His sweet tooth for chaos. But in the end, his well-established unwillingness, or inability, to make and maintain relationships that matter might be the most politically debilitating. Or it might not be. This elemental character trait seen by many as such a liability hasn’t stopped him yet. He is, after all, the most powerful person in the world.

“GOOD!”

“I don’t want them.”

He means it.

***

The first people who really noticed Trump’s tendency to withdraw were his classmates. As a teenager at New York Military Academy, in upstate Cornwall-on-Hudson, he often disappeared into his solo room in the barracks after dinner. “The reason I went in the first place,” Trump himself would say later, “was that I didn’t get along with a lot of people.” Pictures in yearbooks in the library at the school show Trump morphing from a gangly boy to a sturdy young man, but this much didn’t change: Classmate Doug Reichel characterized him to me as “very distant.”

“I don’t know anyone that he was particularly close to,” said Ernie Kirk, a classmate who is now an attorney in Georgia.

“He was so competitive,” according to a former roommate, “that everybody who could come close to him he had to destroy.”

Donald Trump was a middle child who grew up in Queens, later attending New York Military Academy, Fordham University and the University of Pennsylvania—none of which were schools where he made any lasting friendships. | Donald J. Trump Facebook Page | FACEBOOK

“You just couldn’t be friends with him,” said Sandy McIntosh, who was two years younger but knew him from home, too, because their families both had cabanas at the Atlantic Beach Club on Long Island. Trump wouldn’t laugh at his jokes, or anybody else’s, McIntosh recalled. “And you think of humor as a basic, empathic way that friendships are formed—and he just didn’t.”

“I was not a confidant as to his personal thoughts. No one was,” Trump classmate Peter Ticktin wrote not long ago in an email to McIntosh. “He was much to himself. A good guy, but no one’s real buddy.”

In a recent phone conversation, Ticktin, an attorney in Florida and a supporter of Trump, said Trump at NYMA “did have a little touch of aloofness.” But he chalked it up to Trump’s rank early in his senior year as the captain of A Company (“part of being a natural leader is not to be everybody’s buddy”) along with his apparent self-confidence (“he just didn’t need to share his deepest thoughts”)—and Ticktin also attributed it partly to the strict, draconian atmosphere on campus. “He was nobody’s real buddy, but nobody was anybody’s real buddy,” Ticktin said.

It was the same way, though, at Fordham University in the Bronx, where Trump spent his freshman and sophomore years of college playing on the squash team and wearing a three-piece suit to class. Trump and Brian Fitzgibbon sometimes carpooled to school because their families both lived in Jamaica Estates. They were “friendly,” Fitzgibbon said in an interview, but not “friends.” “I can’t recall any real friendships he had at Fordham,” he said. When Trump transferred from Fordham to the University of Pennsylvania, he left without telling people goodbye.

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And it was no different, either, down in Philadelphia, where he studied real estate at the Wharton School of Finance and Commerce and boasted in class that he would be bigger than then-nonpareil Manhattan developer Bill Zeckendorf—but, for the most part, one classmate told the Daily Pennsylvanian, Trump “was really off by himself.” He didn’t participate in extracurricular activities or go to fraternity parties or football games. He returned every weekend to New York to work for his father collecting rents at his outer-borough apartment buildings. “His footprint at Penn was virtually zero,” classmate Lou Calomaris told me. “I don’t think he had any best friends. I never saw him pal around with anyone, quite frankly.”

By 1980, Trump had started to make a name and attractattention, but television interviewer Rona Barrett seemed to sense this defining absence.

Donald Trump poses in his Manhattan office beside a copy of his book, “Trump: The Art of the Comeback,” in 1997. | AP

The whole of the ‘80s were heady for Trump. He built Trump Tower, his masterwork until “The Apprentice” led to the Oval Office. The Art of the Deal was a runaway best-seller, and he talked about running for president. Even his failures, like his ownership of the New Jersey Generals of the second-rate United States Football League, were successes of a sort, because they boosted his national renown, which was actually the point from the start. And yet as ascendant and ubiquitous as he was, Trump was fairly friendless, too.

It wasn’t just high society, said George Arzt, a veteran, connected New York politico. “Most of the real estate industry separated themselves from him,” Arzt told me. “His personality rubbed people the wrong way.”

“Friendship is not a part of his agenda,” a Trump business associate toldNewsweek in 1987. Trump didn’t disagree. “I hate to have to rely on friends,” he said. “I want to rely on myself.” His only “real friends,” he added, were family members.

On newsstands nationwide at the time of this interview was an extensive conversation in Playboy. In it, Trump echoed something he had discussed with Chung, too—the death of his older brother, Fred Trump Jr., and its lasting effects. His brother had been too trusting with too many people, “a fatal mistake,” in Trump’s estimation, and he had been taken advantage of, and that had led to his alcoholism and finally his demise at only 43 years old. “The lesson I learned,” Trump concluded, “was always to keep up my guard one hundred percent, whereas he didn’t.” He ended up later in the interview musing about the prospect of a President Trump. “He wouldn’t trust anyone,” Trump said.

“More than condos or casinos, he’d spent his life building defenses—walls to fend off the people around him,” Wayne Barrett (no relation to Rona) wrote in 1992 in his seminal early biography of Trump. Even the people closest to him, Barrett said, never “really got past his self-contained wariness.”

Ever since, in Trump’s long arc, these walls and this wariness have made for one of the clearest, straightest through lines.

He thinks the world is “horrible.” He thinks people are “vicious.” He thinks they are ceaselessly envious and want what he has. “Trust your instincts,” Trump has said. “Trust yourself.” But nobody else. “There are so many stories about people who have been decimated by people they trusted,” he has said. There’s nobody he admires. He has no heroes. “Donald,” gossip columnist Cindy Adams once said, “is somebody who’s in love mostly with himself.”

“Being on the other side of a relationship with someone like me must be difficult,” Trump toldPeople in 1997.

Including his wives. “It’s very hard for somebody to be married to me,” he told biographer Michael D’Antonio in 2014.

In The Art of the Deal, Trump called his parents “my closest friends.” When they died—his father died in 1999, his mother a year later—it was the closest he ever came to crying, he later claimed. “I don’t believe in crying,” he said in 2005. “… It’s just not my thing. I have nothing against it when someone cries, but when I see a man cry I view it as a weakness. I don’t like seeing men cry. I’ll give you an example. I never met John Gotti, I know nothing about John Gotti, but he went through years of trials. He sat with a stone face. He said, ‘Fuck you.’”

Some of the people Trump has called friends over the years. | Clockwise from top left: CRAIG LASSIG/AFP/Getty Images; Ron Galella/WireImage; Jeffrey Asher/ Getty Images; Ron Galella/WireImage

Over the years, Trump has labeled many people his friends. Michael Jackson and Jesse Ventura and Tom Brady. Larry King and Don King and Mike Tyson. Newt Gingrich and Sylvester Stallone and Oprah Winfrey and Howard Stern and Elton John. Carl Icahn and Richard Lefrak and Tom Barrack. (“Tom Barrack is to Donald Trump as Bebe Rebozo was to Richard Nixon,” said Stone, who has a tattoo of Nixon on his back.) Often, Trump’s friends don’t respond to requests to talk about the nature of their relationships with him. Sometimes, they have publicists who call to say quietly that they’re not actually friends. Trump has called “Little” Marco Rubio a friend. He has called “Lyin’” Ted Cruz a friend. He has said he has friends in Europe and Australia and China and Japan. He has, he has said, friends who “aren’t Christian,” friends who are Jewish, friends who are Muslim.

“I have many friends,” he said two years later at the Conservative Political Action Conference. “Many, many friends.”

And three years after that, at a campaign rally in New Hampshire heading into its primary vote, he told people he has lots of rich friends—but they wouldn’t be his friends, anymore, if he became president. “I have no friends, as far as I’m concerned,” he said, an applause line, a laugh line, but a line that struck students of Trump as unwittingly spot-on.

“You know who my friends are?” Trump said. “You’re my friends.”

The cheering crowd.

***

All presidents, as Roger Stone said, grapple with loneliness. It’s a function of the gravity of the position, having to make hard choices nobody else has to or can. But President Trump arrived with the affliction. Looking at the situation in Washington, and thinking back to the college student he knew, Calomaris from Penn invoked Heraclitus, the Greek philosopher, and his most known maxim. “Character is fate.”

For Nixon, Calomaris said, it was his paranoia.

Bill Clinton, he said, thought with “the wrong head.”

With Trump, will isolation be his undoing?

Chris Ruddy has been friendly with Trump for nearly 20 years. The Newsmax CEO and Mar-a-Lago member considered my questions about the president. “You know Harry Truman’s famous line?” he said. “You need a friend in Washington …” Get a dog. (Truman didn’t actually say that, but the point stood.) “He doesn’t need to have close friends,” Ruddy said.

It’s not that simple, Stone said. The trouble, as he sees it, is not that Trump has few friends in Congress, or in the GOP, least of all leaders Mitch McConnell and Paul Ryan. “Under no circumstances,” Stone said, “should he consider those guys his friends. That’s a business relationship. Their interests are very different than his.”

Rather, Stone continued, the more pressing issue is that Trump is increasingly isolated within his own White House. “If he has friends,” Stone said, “his friends should be in his administration. I guess my greatest criticism would be he has hired people and appointed people who are not his friends. Didn’t vote for him. Don’t share his worldview. Aren’t necessarily interested in his long-term success.”

Stone added: “It’s not clear to me if he understands the dangers and potential damage that’s posed by surrounding himself with people who are not loyal to him—but, more importantly, not loyal to his agenda.” He named H.R. McMaster. He named Gary Cohn.

“He’s very much his own man,” Stone said of Trump. “This is not a guy who’s ever told what to do, what to say, where to go, who he can meet with, who he can’t meet with, who he can talk to, who he can’t talk to, where he can travel to. He’s really a free spirit and he deeply resents attempts to handle him or manage him or control him. Which is why ultimately I believe General Kelly will fail.”

I asked him if he thinks Trump trusts Kelly.

“Today,” Stone said.

I asked him if he, too, like Trump himself, thinks Trump has trouble trusting anybody.

Nonetheless, when Trump needs friends, or new friends, he can make them, Ruddy reasoned. “I think he saw the presidency as more of a monarchy,” Ruddy said. Realizing by now that it’s not, he’s capable of creating necessary relationships, according to Ruddy—talking days before Trump started dealing, or “beaming and scheming,” as his first wife once said, with Democratic leaders Nancy Pelosi and Chuck Schumer, whom he’s called a “clown.”

“I think he’s ultragifted in the things in politics you need for relationship-building,” he said. “He’s an impresario at this stuff.” Added Ticktin, the pro-Trump NYMA classmate: “Normal socializing with people, I don’t think that’s ever really been his thing. But he knows how to work a room. He’s charming, and he knows how to connect with people in a room and make them feel like they’ve been acknowledged.”

This, though, is a variant of the gap between campaigning and governing, politicking and legislating. Trump self-evidently can do the former. It remains unclear whether he’s capable of the latter—the give-something-to-get-something, the slow build of capital that then can be cashed in, not flimsy, news-cycle-feeding insta-alliances but the long-game cultivation of critical relationships.

“He’s fundamentally a loner,” said O’Brien, the biographer. “Along the way”—his whole life—“he hasn’t forged deep bonds with other people.”

And that’s what’s been playing out during his presidency, something that was noted early and has been crescendoing ever since, as his original staff—and at least one replacement—has been thinned by firings and resignations.

“He seems both politically and personally isolated these days,” David Gergen told the Washington Post in April. “He doesn’t have anybody whom he trusts,” someone who speaks with the president told CNN in May. “He’s much more isolated than he realizes,” Newt Gingrich told Fox News in August. “The narcissism and paranoia are issues, but the biggest concern is that Donald Trump trusts no one,” Gail Sheehy writes in a forthcoming compilation of essays, The Dangerous Case of Donald Trump: 27 Psychiatrists and Mental Health Experts Assess a President. “This will be his downfall—or maybe ours.”

Louise Sunshine is worried. She’s known Trump longer than almost anybody alive. She was a vice president for the Trump Organization from 1973 to 1985. I asked her if she thinks he’s feeling isolated.

“Definitely,” she said.

“He isolates himself when he finds it convenient,” Sunshine went on. It’s what he’s always done. “Always.”

In particular at the points of the greatest duress. Periodically over the past few months, and especially over the past few weeks, I have found myself thinking back to 1990. It’s the moment before the current moment when Trump seemed the most isolated and alone. His business was listing, and he was losing inner-circle loyalists. “It’s come to be Donald against the world,” an adviser told biographer Gwenda Blair at the time. His marriage was over. His oldest son, then 12, angry and hurt, wasn’t speaking to him, it would later be reported. In telephone public opinion polls, readers of New York tabloids were siding overwhelmingly with his wife, not him. “When a man leaves a woman, especially when it was perceived that he has left for a piece of ass—a good one!—there are 50 percent of the population who will love the woman who was left,” Trump raged to Marie Brenner of Vanity Fair.

But past the familiar, reflexive bombast, the early portion of that year always has seemed to me to be an unusual and even unique stretch in the scope of Trump’s life. Rewatch that Connie Chung interview, and reread that Playboyconversation, and he presents as not only irritable but rattled—vulnerable, or at least his version. Even his book that came out in 1990, Surviving at the Top, is in my mind different from all the other books he’s put out over the decades, so many same-sounding collections of business tips and self-help schlock. It has plenty of platitudes, too, but there’s also in the text and between the lines a certain detectable pathos. The title itself is an amalgam of a plea and a lie. That spring, according to Vanity Fair, Trump holed up in Trump Tower, in an apartment separate from his soon-to-be-ex up in the penthouse, ordering in burgers and fries from New York Delicatessen, his belly getting soft, his hair getting long, staying on his back in his bed, staying up late, calling people to talk, staring at the ceiling.

“You remind me of Howard Hughes,” a friend told him.

“Thanks,” Trump said. “I admire him.”

He wrote about the tycoon turned neurotic hermit in Surviving at the Top. “The Howard Hughes story is fascinating to me,” Trump told readers, “because it shows that it’s possible to fall very far very fast. As time goes on I find myself thinking more and more about Howard Hughes and even, to some degree, identifying with him.” He cited Hughes’ aversion to germs, and the downsides of fame, like when he’s approached in restaurants and people end up “spraying their good wishes all over my food.”

“Every time that happens,” Trump wrote, “Howard Hughes and his reclusive lifestyle look a little less crazy to me.”

Wayne Barrett addressed Trump’s interest in Hughes in his biography. Barrett had been reporting on Trump since the late ‘70s. His book came out in 1992.

“Over the years,” Barrett wrote, “he had openly toyed with a final surreal twist to the plot that had become his life—he told friends that he might end up a Howard Hughes-like recluse, squirreled away, allowing his fingernails to grow longer than his stubby fingers. That poignant script may have appealed to the loner quality in him that had always kept him apart. The Hughes scenario only worked, though, if he could figure out a way back to the top.”